Toni Cipriani

Antonio "Toni" Cipriani (1968 - Present) was a member of the Leone Mafia Family in New York City. He eventually became boss of the family after Salvatore Leone was murdered in 2001.

Biography
Born in New York City in 1968 to Ma Cipriani and an unnamed father, who was a member of one of the city's mafia families. He lived with his Ma in their restaurant and and was regularly beat by her as a child and an adult. He later became involved in Liberty City's criminal underworld, joining the mafia to follow on his father.

Toni left Liberty City and decided to lay low in a foreign country after killing a rival made man (presumably Forelli or Sindacco family) under orders from Salvatore Leone in 1994. He finally returned to the city in June 1998, ready to continue his life of organized crime. A grateful Salvatore Leone gave Toni jobs, but because he was out of town for so many years, other members of the Leone Family had the time to move up in the hierarchy. Salvatore was forced to strip Toni out of his rank and give the position to Vincenzo Cilli during his leave of absence. Toni now found himself as a low-ranking goon that had to once again gain favor with the Don, in order to secure a leadership position in the family. Toni however worked for Salvatore's wife Maria Latore who later on, developed feelings for Toni and had him to do her bidding, and told him she loves him, but Toni didn't not feel the same way. However, after she learned Toni "has no money", she cut ties with Toni, reminding him that she is Salvatore's girl and not to hit on her. Much of his efforts in achieving his goal of reclaiming his place in the Leone hierarchy included battling two other Mafia families, the Forellis and the Sindaccos via several means, allowing him to be "made" after killing the New York City mayor, Roger C. Hole. After being made, his mother called off a hit she had put on her son. Later, Toni worked for millionaire and mayor candidate, Donald Love and fought the Forelli's in order to help the Leone's own City Hall while protecting Donald. Donald Love eventually was found to be in league with Salvatore and Toni, which made him unfit for the office in people's eye. After Miles O'Donovan had been elected mayor, Salvatore Leone was arrested on several crime charges, forcing Toni to pose as a lawyer named Lionel to take jobs from the police station where Salvatore was imprisoned.

Donald Love, in a stressful phone call, said that he had many propositions for him. Upon arriving at the flophouse, Donald Love says that he has plans that will make both Toni and himself rich again and ordered Toni to kill real estate businessman, and Love's former mentor, Avery Carrington. Toni and Donald stole Avery's plans and bomb expert 8-Ball was paid to give them explosives in order to blow up Fort Staunton, causing the Forelli Family to lose a lot of influence. Toni was called by a mysterious woman, Toshiko Kasen, and asked to fight the local Yakuza organization. After Toni killed her husband Kazuki, a remorseful Toshiko committed suicide and a panicked Donald Love asked Toni for some help to take him to Francis International Airport as the Colombian Cartel were attacking to steal Avery's plans. Toni got Love to the airport safely and Love brought with him the corpses of Avery Carrington and Ned Burner.

Salvatore was eventually released from jail, after being escorted to the courthouse by Toni, due to the Sicilian Mafia wanting Salvatore dead. After being released, Toni and Salvatore went to see the mayor, Miles O'Donovan, to get his charges dropped. However, Massimo Torini, a high-ranking member of the Sicilian Mafia, had the mayor kidnapped. Toni and Salvatore chased Torini and rescue the Mayor from Portland Rock, killing Torini in the process.

By 2001, Toni had become one of the highest-ranking members of the Leone Family, behind only Salvatore Leone. The police had attempted to connect Toni and Salvatore throughout 2001; however, they fail to link them beyond his mother's restaurant. Salvatore’s son, Joey, introduces the game’s protagonist, Claude, to Toni. Toni hires Claude to attack the Triads (Leone Family enemies), including trying to get protection money from Mr. Wong's Laundromat, destroying some Triad fish vans and the Triad owned fish factory in Callahan Point. Toni also introduces Claude to Salvatore Leone.

In 2001, Toni was still working with his mother and was frequently seen in his family-run restaurant, where he provided Claude with jobs. The constant insulting from his mother about him not being able to be like his father and failing to meet up to her expectations had forced him to call the local chat radio station, Chatterbox FM, and complain about his mother's constant berating. He took over as boss of the Leone Family after Salvatore's death that same year.